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The Strong ?-CF3 Shielding Effect in Hexafluoroisopropanol and 100 Other Organic Solvents Revisited with 17O?NMR Spectroscopy.

ABSTRACT: An 17O?NMR spectroscopy survey of more than 100 ubiquitous organic solvents and compounds, including some typical oxofluorinated solvents such as hexafluoroisopropanol, trifluoroethanol, trifluoroacetic acid, and others, is presented with D2O as a reference. A strong alternating ?,?-CF3-substituent chemical shift effect was thus observed. This alternating deshielding-shielding effect is suspected to have a role in the exceptional properties of these oxofluorinated solvents, notably in oxidative cross-coupling reactions.

SUBMITTER: Bernhardt A

PROVIDER: S-EPMC5915748 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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The Strong β-CF3 Shielding Effect in Hexafluoroisopropanol and 100 Other Organic Solvents Revisited with 17O NMR Spectroscopy.

Bernhardt Annika A Kelm Harald H Patureau Frederic W FW

ChemCatChem 20180223 7

An 17O NMR spectroscopy survey of more than 100 ubiquitous organic solvents and compounds, including some typical oxofluorinated solvents such as hexafluoroisopropanol, trifluoroethanol, trifluoroacetic acid, and others, is presented with D2O as a reference. A strong alternating α,β-CF3-substituent chemical shift effect was thus observed. This alternating deshielding-shielding effect is suspected to have a role in the exceptional properties of these oxofluorinate ...[more]

PMID: 29731952

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